


If the Shoe Fits

by LeafZelindor



Category: Supernatural
Genre: Bottom Dean Winchester, Dean has sex with a pair of shoes, Dean likes Hentai, Drag Queen Dean Winchester, Other, PWP, Tentacle Porn, strange magic is afoot
Language: English
Status: Completed
Published: 2018-12-16
Updated: 2018-12-16
Packaged: 2019-09-19 19:25:56
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,439
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17007729
Author URL: https://archiveofourown.org/users/LeafZelindor/pseuds/LeafZelindor
Summary: When Dean does Drag he enjoys himself. He has a favorite pair of shoes. They're uncomfortable, but they're fun, they are tentacles. One night, the shoes come to life, and show him exactly how much they love him too.





	If the Shoe Fits

**Author's Note:**

> Okay this is total crack. Written for my pervy friends in ProfoundBond on discord. Inspired by the shoes found here:  
> https://starsinursa.tumblr.com/post/181138759634/emilreloaded-hogwartsconsultingtimelady 
> 
>  
> 
> Warning this has only been looked over once. lmao. Enjoy my tentacle porn.

A few times a month, Dean sheds his typical flannel, his jeans, his heavy steel toe boots and he transformed into the most beautiful, Impala Drama. Yeah, sure there was latex involved, and he usually had to shave his legs, and he’d learned a hell of a lot about how to do make-up, but it was worth it. The chance to take a night and be someone else. To dress himself up and be genuinely beautiful, it was amazing. Nobody judged him these days, and it was fun to see how ridiculous he could get. 

Somehow though, he’d managed to obtain a pair of beautiful, and yet absolutely ridiculous shoes. They were open toe, and created out of lovely twisted tentacles, but the way they framed his feet when he wore them made him feel intensely bold, extra confident. While they were uncomfortable to wear for a very long time he found himself pulling them out every two months or so and wearing them anyway. When he wore them he felt even more graceful than ever. He’d found a perfect flowy seafoam green dress to go with them and he wore a wig that reminded him of Ariel from the little mermaid, with purple accent jewelry and eye shadow. Dean always had a good night when he went out in those delightful, ridiculous shoes. Tonight had been no exception. He had left the shoes out on his bed as he’d undressed and gone to clean up. He was fresh from the shower, a towel tucked around himself as he moved to sit down, fingers rubbing over one of the lovely tentacles. It was almost a shame to put them up in their box again.

“Maybe I’ll just put you away tomorrow morning, you pretty things,” he murmured as he sighed a bit, finger hooking through one of the open spaces as his thumb rubs over the fake suction end. Dean moved to pick up the shoe and then he startled and almost dropped it. One of the tentacles had moved, curling around his fingers. His green eyes widened now as he felt it stroke over his skin. 

“What...The fuck…” Dean breathed out. The tentacles were really moving now, sliding over his hand and then around his wrist in moments, and a shiver going up his spine from the touch. His eyes flicked to the other shoe, it too was moving now, sliding across the bed, the tentacles reaching for the edge of the towel where it rested on his legs. 

“Oh my fucking god.” He gasped now, the ones around his wrist stroked soothingly now and he licked his lips nervously, but excited to. 

It was strange how easily he let himself settle back. Dean didn’t know what gender shoes saw themselves as, but they certainly seemed to know what they were doing. The first shoe had more or less untwisted twisted itself and was sliding slowly up his arm, the other was still trying to get under his towel, and his cock? It was certainly taking some interest, hardening visibly under the soft cloth. 

Now Dean was no stranger to some very interesting forms of hentai, but he’d never thought he’d actually, be in one. It was fascinating, the slightly slick feeling going up his inner thigh. The way the other shoe was warm as it crept up his arm and flicked just under his ear like a kiss. The sort of thing that made his eyes flutter half closed and his lips part with a soft pant. He loved when that part of his neck was teased. 

The other shoe, the one mostly under the towel was almost against his mostly hard cock, then it was there, one tentacle was curling around his cock and, fucking pulsing, flexing a bit, it had coiled along his length in a moment and was working him over. His legs slowly spread somewhat, curious and he let out a soft little squeak as he felt something prodding his asshole, another tentacle he was sure. 

“F..Fuck..Yeah, okay,” Dean breathed and he felt it breach him properly. It was just as oddly sort of slick as it had felt going up his thigh. He could feel other ones wiggling under the fabric and then he reached down, wanting, aching to see what it looked like really as he pulled the towel away. He was rewarded for his curiosity, the way that the first tentacle was curled around his cock looked, gorgeous really, It flexed and wiggled over him stroking in it’s own way. The other, he couldn’t see but he could feel it pushing into him, slow, rhythmic. It didn’t feel anything like a finger would. It felt better than any finger if he was honest, spreading him slowly, wiggling inside of him teasing. 

Dean found himself crying out softly as the one that had crawled up his arm reached out and flicked a nipple. His hips rolled up somewhat now, against an invisible thing, the tentacles themselves were moving on their own, the one inside of him thrusting slowly, pulsing some properly. He took a breath and then he found he was whimpering again, as he slowly rolled up into the air. 

“M..more?” Dean asked now, It seemed like the tentacles that made up his shoes knew just about everything he liked. He didn’t even have to say it. There were soft flicks over his nipples, both of them now. That was quickly followed by the sensation of another one pushing into his ass, two of them spreading him, as if preparing him for more. Dean felt a full shudder go through him and he let his fingers dig into the bedding. He rocked up once more, lifting his hips against an invisible something as the tentacles thrust into him, two, then three. He panted harder, a sheen of sweat starting to appear on his forehead. The one around his cock tightened, holding him back from anything too much as one more pressed a bit deeper, finding that sweet spot that made Dean yelp and then buck up. “Fuck!” 

Two tentacles slid up over Dean’s jaw and his lips parted almost instantly to allow them in, letting them fill his mouth. He sucked on them, it was a strange sensation, They didn't’ feel like a cock, and there were two but it was easy to suck, easy to let them start to fuck his mouth the same way that the others were in his ass. Turning him into a moaning mess. 

It seemed like Dean was completely out of control now. Needy, panting, feeling the squirming inside of his ass, the flicks over his nipples, occasionally against other parts of his skin, teasing him in a way that he hadn’t had a lover touch him in years. He’d lost track of how many tentacles had pushed into his ass but he could feel it, each thrust, each rubbing inside of him as they filled him completely, making him feel so full and making him beg needily for release. 

The one around Dean’s cock flexed, starting to coax now, stoking in a rolling fashion that if he’d been able to focus would have looked very interesting against his skin. Instead his eyes were screwed shut as Dean kept sucking on the tentacles in his mouth. Dean was completely unable to focus because of the intensity of the pleasure he was feeling that suddenly it was there, he was coming, crying against the tentacles in his mouth, the familiar spatter of cum on his stomach as his ass when tight around the pulsing and wriggling tentacles. 

Dean was dazed and went fully limp in a few moments. The tentacles in his mouth slipped away and he was able to pant full mouthed, gulping down air. He shuddered as the others started to slide from his body, he blinked hazily, not quite processing the feeling of the tentacles stroking his skin, petting him almost. He let his eyes close slowly and just relaxed. He just needed a minute. 

Just a minute. 

When Dean finally woke there was no sign that the Shoes had been anything but shoes. They were resting next to him on the bed, on their sides, half dried cum was tacky against his skin, the only evidence that anything had happened. He’d almost be able to swear it hadn’t really happened, except when he reached out to touch one of the shoes, he could almost swear it pulsed under his fingers. Dean swallowed slowly now, unable to help wondering if something quite so fun would ever happen again.


End file.
